Synthesis of Poly(vinyl alcohol)s Having TEMPO Units in Their Pentant Groups

A condensation reaction of p-formylbenzoic acid and 4-hydroxy-2,2,6,6-tetramethylpiperidine using 1,1'-carbonyldiimidazole in DMSO at 80°C for 48 h produced the ester (p-FB-TEMP-H) in a 64% yield. The acetalation of the formyl group of p-FB-TEMP-H with poly(vinyl alcohol) (PVA) in the presence...

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Bibliographic Details
Published in:KOBUNSHI RONBUNSHU 2009, Vol.66(11), pp.524-526
Main Authors: SATO, Rikiya, KATSUMATA, Yoshihiro, KIRYU, Yasuhiro, IKEDA, Yasuhiro
Format: Article
Language:Japanese
Subjects:
1,1'-Carbonyldiimidazole
Acetalation
p-Formylbenzoic Acid
Poly(vinyl alcohol)
TEMPO
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Summary:A condensation reaction of p-formylbenzoic acid and 4-hydroxy-2,2,6,6-tetramethylpiperidine using 1,1'-carbonyldiimidazole in DMSO at 80°C for 48 h produced the ester (p-FB-TEMP-H) in a 64% yield. The acetalation of the formyl group of p-FB-TEMP-H with poly(vinyl alcohol) (PVA) in the presence of acetic acid as an acid catalyst yielded the corresponding acetals of PVA and p-FB-TEMP-H (PVA-p-FB-TEMP-H). The introduction rates of p-FB-TEMP-H onto PVA were calculated from 1H NMR results of the products. The rates of the acetalation based on PVA monomer unit were about 1.5-19%. The oxidation of PVA-p-FB-TEMP-H with H2O2 using sodium tungstate as a catalyst converted the piperidinine ring into a 2,2,6,6-tetramethyl piperidine-N-oxyl (TEMPO) structure. The ESR measurements of the polymer radicals obtained showed strong signals in good solvents for PVA but not in poor solvents for PVA. These results indicate the introduction of a TEMPO structure onto PVA.
ISSN:0386-2186
1881-5685
DOI:10.1295/koron.66.524